I'll take a stab at some of these.
The title companies will typically allow you to put your deposit on a credit card and then you will pay the balance by cashier's check or wire transfer.
You only pay the deposit when you sign the contracts (then the contract is sent to Disney for ROFR). The rest of the balance will be due at closing. If Disney takes the contract, you can either get a refund, or let the title company keep it for your next contract attempt.
I won't get into the ethics of what you're proposing. But if you do that, you will forfeit your deposit on that contract.
Either works.
If you cancel less than 31 days before you're trip, your points will go into holding. Which means they can only be used to make reservations 60 days before check-in.
DVC is NOT a good option if you think there is a chance for several last-minute cancelations.
If you buy resale, you can use your points at any DVC resort (AKV, BCV, BLT, BWV, VWL, VGF, OKW, SSR and Hilton Head, Vero Beach and Aulani (Hawaii)). You can also use your points to trade into RCI to stay at other destinations (but be aware that DVC only allows for trades a fraction of RCI's properties).
You can't use your points for
Disney Cruise Line, Adventures by Disney or the Disney Collection (non-DVC Disney resorts).
You will buy a contract at a specific resort, that is your home resort. You can book your home resort at 11 months out from check-in. You can use your points at any of the DVC resorts starting at seven months before check-in.